Shawn is an experienced commercial litigator who focuses on delivering value to Osler’s clients in their high-stakes business disputes. Whether acting on a complex multi-jurisdictional class action, a contested dispute over the dissolution of a private company, or the restructuring of an insolvent company, Shawn tirelessly advocates for those he represents while remaining committed to obtaining the best practical results.
Shawn acts predominately for corporate, banking and other financial sector clients, and has significant expertise in the insolvency and restructuring and private equity and investment fund space. He regularly represents clients in securities, commercial and insolvency proceedings, as well as in investigations and enforcement proceedings involving various securities regulators. Some of Shawn’s recent non-confidential mandates have included representing Nieuport Aviation in obtaining a judgment of over $130 million against Porter Airlines; defending Manulife Financial in several multi-jurisdictional class actions; representing certain former directors and officers of Wayland Group in a proposed class action; representing Corus Entertainment in its successful response to an OSC application; successfully defending a shareholder rights plan; and defending Royal Bank of Canada in a class action brought by retail investors following the collapse of a major offshore investment fund. Shawn has also acted as debtor counsel in numerous Companies' Creditors Arrangement Act (CCAA) and Bankruptcy and Insolvency Act proceedings, including CanWest, Target Canada, Sears Canada, Just Energy, Bondfield, Brooks Brothers, Comark, Ted Baker, Phoenix Brands, Hollander Sleep Products and SFP Canada d/b/a Papyrus. He has also acted in several high-profile receivership proceedings.
Personally invested in identifying innovative solutions for clients, Shawn is a current member of Osler’s Innovation Council, where he works to drive efficiencies, predictability, and lower costs for clients. Shawn has supported the development and execution of Osler’s adoption of cutting-edge technology in the legal space, including AI, service delivery improvements, and the broad and creative use of Alternative Fee Arrangements
Shawn was named a “Rising Star” by Lexpert magazine in 2014, a “Litigation Lawyer to Watch” in 2015, a “Future Star” by Benchmark Litigation, and is recognized in the area of Corporate and Commercial Litigation by Best Lawyers in Canada.
Areas of Expertise
Representative Work
Insolvency and Restructuring
- Represented Comark Holdings Inc. Bootlegger Clothing Inc., cleo fashions Inc. and Ricki’s Fashions Inc. in their successful restructuring proceedings commenced in the Ontario Superior Court of Justice under the CCAA.
- Represented Target Canada Co. on all aspects of the complex and high-profile wind-down of its Canadian operations, including the development and implementation of restructuring strategies, stakeholder negotiations, and court proceedings under the Companies’ Creditors Arrangement Act (CCAA), one of the largest retail insolvencies in Canadian history.
- Counselled for KEB Hana Bank, as trustee of IGIS Global Private Placement Real Estate Funds, in the high-profile, $1.2 billion receivership proceedings commenced against Mizrahi Development Group Inc., Mizrahi Commercial LP, and Mizrahi Commercial GP Inc, the developers behind The One, an 85-storey mixed-use skyscraper at Yonge and Bloor in Toronto.
- Represented Ted Baker Canada and Ted Baker Limited in its successful wind-down of operations in North America under the CCAA and Chapter 15 of the United States Bankruptcy Code.
- Represented Just Energy Group Inc. in connection with its $1.1 billion recapitalization transaction, including in connection with a contested claims dispute relating to the termination of certain complex derivatives.
- Represented Bed Bath & Beyond Canada in its proceedings under the CCAA to facilitate the orderly wind-down of Canadian business, including 65 stores.
- Represented KPMG in its capacity as Court-appointed Monitor of Crown Crest Capital Corp., Crown Crest Financial Corp., Crown Crest Funding Corp., Simply Green Home Services Inc., Simply Green Home Services Corp., and Crown Crest Capital Trust, in proceedings commenced in the Ontario Superior Court of Justice under the CCAA.
- Acted as counsel to David’s Bridal, including David’s Bridal Canada Inc., in connection with its proceedings in the United States under Chapter 11 of the United States Bankruptcy Code and in Canada under Part IV of the CCAA.
- Represented SFP Canada Ltd., a leading retail chain, in its CCAA proceedings, guiding the company through operational restructuring, asset realization, and negotiations with secured and unsecured creditors to achieve a successful outcome.
- Represented PricewaterhouseCooper in its capacity of court-appointed liquidator of Silicon Valley Bank (SVB) in respect of its winding up of its business in Canada under the Winding Up and Restructuring Act (WURA).
- Represented Phoenix Brands Canada, Payless Shoes, Hollander Sleep Products, Jack Cooper Ventures, and BBGI Canada (formerly Brooks Brothers Canada) in their respective cross-border insolvency matters under Part IV of the CCAA.
- Represented Bondfield Construction, one of Canada’s largest construction firms, in its high-profile CCAA proceedings, including the development of restructuring plans, resolution of significant claims, and the preservation of ongoing projects.
- Acted for Wayland Group Corp., a publicly traded cannabis company, throughout its CCAA proceedings.
- Represented Sears Canada Inc. in its landmark CCAA proceedings, providing comprehensive legal support on restructuring, liquidation, and stakeholder engagement in one of the most significant retail insolvencies in Canada.
- Successfully acted for Equity Ventures International Holdings Ltd., a major creditor of CanaSea Oil and Gas Group Pte. Ltd., in a precedent-setting case that resulted in the termination and declaration of void ab initio of a CCAA Initial Order.
- Advised CanWest Global Communications Corp. in its successful restructuring under the CCAA, assisting with the development and implementation of a court-approved plan of arrangement, stakeholder negotiations, and the preservation of media operations during a period of significant industry disruption.
Litigation and Dispute Resolution
- Acted for Nieuport Aviation Infrastructure Partners in securing a judgment exceeding $130 million against Porter Airlines in the high-profile case of Porter Airlines Inc. v. Nieuport Aviation.
- Represented shareholder in a claim against Bitbuy Technologies and WonderFi Technologies related to alleged erroneous escrow conditions placed on a shared agreement following arrangement transaction.
- Represented Manulife in proposed class action proceedings commenced in British Columbia, Ontario and Québec concerning the distribution of mortgage insurance products by its wholly-owned subsidiary, Benesure Canada Inc.
- Advised TerraFarma in its acquisition by Aurora Cannabis, a transaction valued at up to $68 million.
- Acted for AltaCorp Capital Inc., as financial advisor to CanniMed Therapeutics, in connection with its acquisition by Aurora Cannabis Inc.
- Counselled Canadian Oil Sands Limited in its agreement to support Suncor Energy Inc.’s amended offer, a transaction valued at $6.6 billion.
- Represented Shoppers Drug Mart Corporation in a class action brought by pharmacist operators of Shoppers Drug Mart stores.
- Acted for Corus Entertainment Inc. in its successful response to an application before the Ontario Securities Commission by The Catalyst Group Inc., relating to Corus’ proposed acquisition of Shaw Media from Shaw Communications Ltd.
- Represented Canadian Oil Sands Limited before the Alberta Securities Commission, successfully resisting an application by Suncor Energy Inc. to immediately cease trade the poison pill adopted by COS in response to Suncor’s take-over bid.
- Successfully represented Jazz Aviation in a complex cost benchmarking arbitration against Air Canada.
- Acted for Asian Coast Development (Canada) Inc. in successfully defending against a $24 million damages claim brought by two New York hedge funds under the oppression remedy provisions of the Canada Business Corporations Act (CBCA).
- Successfully represented the Greater Toronto Airports Authority and the Ottawa Macdonald-Cartier International Airport Authority in an aircraft seizure dispute arising from the insolvency of Skyservice Airlines.
- Acted for RBC in a class action brought on behalf of Canadian and offshore retail investors who suffered investment losses following the collapse of a major offshore investment fund.
Latest Insights
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Blog August 1, 2024
Supreme Court of Canada decision impacts Securities Commissions’ ability to collect from bankrupt transgressors
On July 31, 2024, the Supreme Court of Canada ruled on whether financial sanctions imposed by securities regulators are dischargeable through...
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Blog May 18, 2022
OSC outlines regulatory goals in Statement of Priorities for FY2022-2023
Osler lawyers provide their analysis of the Ontario Securities Commission’s recently published Statement of Priorities assessing issues facing...
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Blog June 24, 2021
Ontario Superior Court dismisses $4.5B negligence claim against TD Bank related to fraudulent Ponzi scheme
Osler’s Shawn Irving, Frédéric Plamondon and Sarah Firestone comment in their latest blog post on the Ontario Superior Court of...
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Webinar April 7, 2021
A New Path Forward: Exploring the Recent Amendments to Ontario’s Class Action Legislation
For the first time since the Class Proceedings Act came into force, the Ontario legislature has made significant changes that have the potential to...
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Awards and Recognition
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Best Lawyers in Canada: Recognized in Corporate and Commercial Litigation
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Benchmark Litigation Canada: Recognized in Dispute Resolution (Future Star)
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IFLR 1000: The Guide to the World’s Leading Financial Law Firms: Recognized in Restructuring and Insolvency (Notable Practitioner)
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Legal 500: Recognized as a Leading Individual in Dispute Resolution: Ontario
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Thomson Reuters: “Stand-out Lawyer”
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Lexpert Magazine: Recognized as a “Rising Star” (2014) and “Litigation Lawyer to Watch” (2015)
Media Mentions
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Osler News May 2, 2025
Osler recognized for outstanding bench strength in the 2025 Benchmark Litigation Canada Guide
Osler is proud to announce that 31 of our lawyers have been recognized in the 2025 edition of the Benchmark Litigation Canada Guide, Benchmark’s...
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Media Mentions April 28, 2020
Remote shifts in Ontario courts are for the better and should become permanent, judicial leaders say – The Globe and Mail
Courts in Ontario have been forced to largely transition from a paper-based, in-person system to a remote operation due to the COVID-19 pandemic, but...
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Osler News January 27, 2020
29 Osler lawyers recognized in Benchmark Litigation 2020
Osler is proud to announce that 29 of our litigation lawyers appear in Benchmark Litigation’s 2020 issue of Benchmark Canada, their annual...
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Osler News March 7, 2017
Osler’s Get Smart: Legal Innovation and Technology Expo showcases how tech is disrupting legal sector
Technology is disrupting the legal sector at a rapid pace and is transforming the way law firms deliver legal services.
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Community Involvement
- Journalists for Human Rights, Various Legal Assistance
Speaking and Writing
Speaking Engagements
A New Path Forward: Exploring the Recent Amendments to Ontario’s Class Action Legislation
Read morePublished Work
- National Insolvency Review, Volume 35, No. 3, June 2018.
- The Advocates’ Society, speaker, Hitting Your Stride education program, June 1, 2016.
- Sealing Orders Since Sierra Club: Effective Ways to Obtain Expansive Confidentiality Protections, Commercial Litigation, Volume XV, No. 3, 2013.
- The Public Interest: Friend or Foe of the Ontario Capital Markets?: A Review of Section 127 of the Securities Act (Ontario), 2nd Annual US/Canadian Cross-Border M&A Forum, New York, NY, April 2007 (with Mark A. Gelowitz).
Credentials
Education
- University of Western Ontario, LL.B.
- Queen’s University, B.A.H.
Languages
- English
Professional Affiliations
- ADR Institute of Canada
- Canadian Bar Association - Ontario
- Law Society of Ontario
- Advocates Society